Ready Whenever You Are
by SoulfulSam
Summary: John is away on a hunt, leaving the boys alone for a week and Sam thinks it's a good time for them to have their first time together. Except, Dean's not so sure Sam's as ready as he thinks he is. Pre-series Weecest, Sam is almost 17
1. Chapter 1

This is a belated Christmas gift for my lovely, darling, wonderful **MJLove1**, who wanted slightly underage Weecest. I also want to thank **Twinchester Angel**, who is awesome and wonderful in every way, for all her time and terrific advice with this story. This is my first time writing the boys so young, so I hope it works. Anyway, I hope you all like this and reviews are love!

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As Dean felt a moan push past Sam's soft, wet, kiss-swollen lips and into his mouth, he leaned back against the headboard of the bed, gripped Sam tighter and thought about how for once he was _so_ not sorry that their dad had left him behind on a hunt. Sam inhaled sharply and shifted closer so that he was straddling Dean's left thigh. They were both in only t-shirts and boxers, so as Sam's erection poked him, he felt the slicked-up cotton of Sam's boxers leave a wet-spot on his naked thigh. He reached down and rubbed his thumb against the tip through the boxers, feeling how the soaked cotton clung to the head. In response Sam fisted his t-shirt and pushed him back harder against the headboard and Dean scooted down on the bed so he could lie down and then grabbed Sam's t-shirt so he could pull him on top of him. Sam got onto his knees, straddling Dean's lap and with his hands resting on either side of Dean's head. Sam's cock was hanging down and just barely brushing the naked skin of Dean's erection that was peeking out from his too-tight boxers and Dean raised his hips to find some friction for them. They'd been making out for over half an hour now, and Sam was moaning at just being barely touched; they were both ready to come.

Instead of rutting against him like Dean expected Sam looked down at their pelvises and then reached down with one hand and pushed Dean's hip down into the mattress, stilling him. Then he brought Dean's hard cock out from his boxer shorts before grabbing his own and starting to rub the head up and down Dean's length, smearing it with pre-cum. Dean watched his cock being slathered by Sam's swollen, red head and the string of clear fluid still connecting their flesh when he pulled back a little and let out a low, primal growl.

"Fuck, c'mere, Sam."

He pushed down on Sam's ass and Sam finally lowered himself onto Dean and began rocking against him, rubbing their cocks together. Dean raised his upper half up a little to meet Sam's lips in another kiss, but Sam avoided his mouth and instead began kissing his ear and then slowly moved down to his jaw and then his neck, working his tongue in a circle around the skin as he covered it with passionate kisses. The heat between their bodies was beginning to make the room hot and Dean felt his skin begin to flush as he and panted and moaned under Sam's attention.

"Are you getting close yet?" Sam asked in between wet, sloppy kisses.

"Not yet Sammy, why? You wanna make this quick, gotta study or something?"

Sam was lightly sucking the skin on Dean's neck when he said that and he could actually feel Sam smile against his skin. "Not tonight."

"Then what?"

Sam stopped rutting his body against Dean's, then slipped his hands underneath Dean's t-shirt, pulling it up over his chest and scooted down on the bed so he could slide his mouth over Dean's right pec. "I wanna make you feel good."

As soon as the words were out of Sam's mouth, Dean knew what he was planning to do and he threw his head back on the pillow as his penis spent a moment warring with his conscience. "You always make me feel good, Sammy, you don't hafta –"

"I know." Sam managed to successfully pull Dean's shirt up high enough so that the fabric was all resting just below his neck and then he came back up for a quick kiss. "I want to." He looked into his eyes and smiled wide, showing his dimples. "I like it."

Dean moaned and closed his eyes as he willed himself to enjoy this and not fight Sam on what he wanted to do. They'd only started going so far as to give each other blow jobs since earlier that week. He'd done it for the first time as soon as their dad left the house to head to a crocotta hunt one state over. Sam was especially worked up at the time because he'd just gotten into another fight with their dad right before he left. This time it was about the school year; it was almost May and school was going to let out in just another month, so Sam wanted to stay in the piece of crap house they'd rented until school was over so he could make friends and pretend he was normal or some shit like that. Of course, Dean had to question Sam's definition of 'normal' because the second their dad's truck was out of view of their rented house Sam had attacked him, so worked up that he was practically mauling him. Sam was more aggressive than usual because he was a combination of angry and horny and Dean felt a little sorry for the kid and wanted to do something special for him. He knew that Sam had never had a blow-job but would definitely like it and, truth be told, Dean had never given head and was a little curious about what it would be like to do it to Sam.

Sam had gasped, moaned, and thrashed against the bed as Dean had worked him with his mouth and then within thirty seconds was pushing Dean's head away, trying to get him to stop as his stomach muscles fiercely twitched and his body tensed for orgasm but Dean had kept going until Sam came apart, his whole body going at first rigid and then completely limp underneath him as he filled his mouth with wave after wave of his bitter, musky, salty come. He hadn't swallowed; he'd planned to, like he'd seen girls do in pornos and like a few chicks had done with him, but there was just a lot of it, it didn't taste that great, and he was afraid that if he swallowed it all it might make him sick. He'd gone to the bathroom and spit it out in the sink, thinking that maybe he could work himself up to it the next time, and then wiped his mouth and came back to their bed. As Sam had lain there, completely sated and weak, Dean had felt proud of himself at how good he could make Sam feel. But then Sam had wanted to do it back. He'd tried telling Sam that he didn't need to return the favor, that the only reason he'd done it was to make him feel good, but Sam had insisted, and now it was already turning into a regular thing. It wasn't that it was bad; Sam was inexperienced but a fast learner and a selfless lover, but there was something about seeing Sam with his cock in his mouth that simultaneously made Dean feel hot and guilty at the same time. Teaching Sam how to talk to girls, change the oil in the car, and properly maintain their weapons was all part of his responsibilities as a big brother but, somehow, showing him how to successfully suck cock, especially his, didn't feel like part of the job description.

But now, Dean's breath hitched and quickened as Sam laved his tongue all over Dean's chest and stomach, laying sloppy kisses all the way down his body, and then grabbed the waistband of Dean's boxers and tugged. Dean arched his back a little to let Sam push them down his thighs and then felt wet heat and light suction on his cock as Sam immediately took the head and about an inch of the shaft into his mouth. As Sam slowly bobbed his head, Dean kept his eyes closed, letting himself just feel the pleasure that was slowly building from his cock and spreading to the rest of his body, making him feel tense and hot all over. Sam's mouth slipped a couple of times as he pulled back, breaking the suction with filthy slurping noises, but he was getting better and better at this every time he tried it and Dean was sure that, this time, if he kept going for long enough he could make him come. Sam pulled off of Dean completely when Dean's chest began to heave.

"Jesus Sammy, you're getting too good at that."

Sam crawled back up Dean's body, kissed him hard on the mouth, and then pushed his tongue inside so Dean could taste the small bit of musky, heady flavor of himself still left on Sam's tongue. Dean grabbed Sam's hair and pulled his head back. He saw the hunger in Sam's eyes and his red, swollen lips upturned into a smile and felt a swell of happiness. He loved seeing Sam look at him like this, so unlike the hungry stares of his past hook-ups who had needed him in the moment when they wanted to get off but the next night would be supplanting his face and body with someone else's. Sam only wanted Dean to satisfy him tonight, and the next night, and the night after that.

"God, look at you, so fucking hot." He pushed down on Sam's ass and raised his hips simultaneously to encourage him to lower himself so that their cocks could touch. "You ready, Sam? You wanna come?" Sam kissed him again, but wrested out of Dean's grasp. Dean sat up on the bed, pulled his boxers back up, and looked at Sam in shock as he slid to the foot of the bed, away from him. Had he done something wrong? "What is it?"

"I…" Sam reached underneath the mattress and pulled out a little brown paper bag. "Well, I went to the store yesterday."

He reached into the bag and pulled out something with a pop-off red top, then grabbed Dean's hand and placed the cool plastic object in his palm and Dean looked down to see that it was a bottle of lube. At first, all he could do was stare at the bottle in amazement. Sam had gone out and gotten this? He couldn't imagine his little brother, who blushed whenever the word 'sex' entered a conversation, walking around a store looking for this stuff. Then Sam reached back into the bag and pulled out a box of condoms and it was only then that all the implications of what was happening really hit him.

Sam set the condoms down beside Dean's left knee. "We – well, I thought now would be a good time for this."

Dean dropped the lube onto the bed beside the box of condoms – Magnums, economy size, Sam must have expected they would have a busy weekend ahead of them – and stared at both disbelievingly. "You want to…"

"Yeah."

Sam had planned, actually _planned_ for them to have sex – he'd gone out and bought – and he could only imagine how red Sam's face must have been when he'd handed the stuff over to the cashier – and now he expected Dean to… He stared at the condoms and imagined sliding one on his cock as Sam lay all opened up and spread out before him and several things happened to him at once; his heartbeat sped up, a surge of guilt made his stomach do a sickening twist, and he dribbled a little pre-cum in his shorts.

Sam followed his eyes to the condoms. "The condoms – I wasn't sure if we were going to actually need them. It's not – I mean, I trust you; I know you haven't been with anyone in a really long time. I just didn't know, you know, if the lube would be enough, that maybe the condoms would make it, well, easier. But we don't have to use them; I know it's supposed to feel better without them."

Dean's stomach tightened and his mouth went dry. Sam was thinking about how he would _feel_ to him, his tight, newly breached muscles squeezing his cock as he moved… Oh god, just the very thought of it, he hadn't had sex in almost six months…He'd wear the condoms – it would still feel awesome and the added lubrication would make things easier for Sam… Before he knew it, he'd allowed himself to picture a whole litany of positions, places, angles – bending Sam over the desk near the front door; sitting on the couch in the living room and holding Sam's hips in place as he rode him; laying Sam down on the bed, on his back and lifting his hips, spreading his cheeks and then lining himself up – before he managed to stop himself. No, Sam was still so young; he wasn't even of voting age yet! He knew Sam wanted this – he never would have touched Sam at all if he even suspected otherwise – but this was a big deal. Sam had never…

Sam slipped his t-shirt off over his head and then crawled into Dean's space, placed a hand on Dean's chest, and gave him a soft, brief kiss. He grabbed the bottom hem of Dean's t-shirt and began pulling it up, but Dean grabbed his hands. "I don't think we should, not yet."

"Then when, Dean? Dad's only going to be gone for another week until my birthday and he's always bringing you along on hunts now; he never leaves us alone anymore. This last time, we didn't even get to touch each other for three weeks!"

"I know! God, believe me, I know. But…it's complicated, Sam."

"No, it's not. We're here. We've got condoms and lube. Dad's not gonna be home for at least a few days. We can do this right now."

"We don't have to have full-on intercourse just because it might not fit into the schedule again for a few weeks! This is a huge step, man. I mean, you're still a virgin –"

"Yeah, Dean, I know. Look, I know it's a big step, but it's one I'm ready to take - we're ready to take. I thought you'd want to."

"I do. Fuck, you have no idea how much I... But Sam, wanting it and being ready for it are two different things."

"I'm not some little kid anymore, Dean; I'm almost seventeen, so don't try to spoon-feed me some crap about being too young for this. You were having sex at fourteen."

"Yeah, and I was way too young for it then too! I shouldn't have lost it then. Fuck, I don't even remember what her name was!"

"Carly Becker."

"You remember that?" Dean was impressed; he wasn't sure he ever knew her last name.

"Yeah, I remember that; I was jealous as hell when I found out. But, that's my point, Dean. I waited and I'm old enough to know that I'm ready and who I want to do this with. I –" his speech faltered for a moment and then he gave him that damn puppy-dog look that always broke Dean's heart whenever he was on the receiving end of it and couldn't give Sammy whatever he wanted. "I want you to be my first, Dean. I always have."

He stared pleadingly into Dean's eyes as he sat up on his knees and pulled down his boxer shorts, lifting one knee at a time so he could pull them down and off his legs. Dean's eyes grew wide and his jaw dropped as he looked down Sam's gorgeous body; the finely-toned muscles that were just beginning to form on his chest, arms, and stomach covered in smooth skin with just a few scars, the v-cut of his hips dipping down to the fine curls of his pubic hair, his muscular thighs and his now semi-hard but still impressive erection standing at attention between them. Sam had grown up into a beautiful man. Dean could feel blood rushing back to his cock and making it grow once again to full hardness. If he did this, it was going to hurt Sammy the first time, and the second too if they had one, but he could be gentle, soft, slow. If he did it right, it would feel really good for the both of them.

He looked back up into Sam's face; the full lips, the little mole beside his nose, his wide, trusting eyes. Sam was giving him the exact same look he did when he was six and Dean told him he was going to let go of the bike handlebars and let him ride on his own, or when he was nine and thought there was a monster in the closet and Dean had told him to climb into bed with him for protection. He swallowed hard. Sam looked up to him and trusted him to do the right thing. He looked up to him because he was the only one who was always there for him, and he trusted him because, other than their dad, he didn't even know anyone else to trust. And now Sam, who griped all the time about hunting, who wanted so badly to be "normal," who knew nothing outside of him, who had seen more death, destruction, and pain in the past few years than most people did their whole lives, trusted him to take away the last shred of innocence he had left. Oh god, what was he thinking? He was going to gently _fuck_ his little brother?

"Sammy…"

"Take me, Dean. Please."

Most people used those words merely as an expression, just another way to say that they wanted to have sex. Sam wasn't; seeing all the love, fear, and vulnerability in Sam's eyes, Dean knew all the implications of what his little brother was saying. He wanted Dean to be his first so he could literally take him and claim him as his. Sex was the last step for them and afterwards, they'd be completely wrapped up in each other. It was everything Dean wanted and nothing that he was ever supposed to have. The room suddenly became small and insufferably hot. There was too much emotion in the air. Dean's throat closed up, his head spun, and his stomach clenched in fear as he stared at Sam. This was – he shouldn't have this, he'd already taken so much from Sam – He'd been a selfish dick for long enough.

"Sam – I – I –" He ducked his head. "I have to go."

He quickly jumped off the bed and began looking for his pants. Sam stared at him, horrified. He grabbed a corner of the blanket and pulled it up over the front of himself. "What? But – but – I don't understand. I thought you wanted this?"

Dean looked at Sam, so openly hurt, the comforter pulled up over him in shame as if he was some kind of hideous monster, and his heart literally hurt at the sight. He felt a pull to go to Sam, to comfort him and hold him, but then the weight of the situation they were in came down upon him, threatening to smother him to death. He pulled up his pants and then grabbed his socks beside them and jammed his feet into them.

"Look, I'll be back later, I just gotta get out of here for now." He slipped back on his t-shirt, threw on his leather jacket, grabbed his boots, and headed for the door to their bedroom.

"Wait! Where are you going?"

Sam's voice cracked on the last word. Dean knew he couldn't turn around, that if he looked at Sam it would all be over and he wouldn't be able to leave. He stood in the doorway and looked down at the ground. "Sam, don't – I'm coming back. I just can't deal with this right now." With that, he quickly left the bedroom, got out of the house, and still holding his boots in his hand, climbed into the Impala, jammed his sock-clad foot onto the accelerator, and peeled out of the parking lot.

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Thanks for reading, the last 2 parts are coming in the next couple of days!


	2. Chapter 2

Fifteen minutes later, Dean settled himself onto a barstool at a dive called Reggie's Tavern. The place was dirty, low-lit, and smelled of cigarettes, vomit, and beer. In the corner, two large and heavily tattooed men played a game of pool, smoking heavily and cursing at each other with every shot the other one took. Hanging back and leaning against the wall to his right, two young women with premature age lines and scars who were dressed in tight, low-cut and high-cut shirts and short-shorts scanned the room, prostitutes no doubt looking for johns. Dean smiled and settled into his seat, feeling at home.

"Bartender!" He called over to the slender woman behind the bar. The short little thing was standing with her back to him on her tiptoes in front of several shelves of liquor and grabbing a bottle of vodka from the top shelf. "Can I get a shot of whiskey over here?"

She turned towards him and he then saw she had a pretty face, complete with a line of freckles across her nose that, along with the short bob-cut of her bleached-blonde hair made her look like a small-town girl next door. Her eyes flashed a look of surprise as she scanned them across his face and then she set the vodka down beside her and shot him a wide, toothy smile. "Whiskey?"

"Yeah, please."

She grabbed a bottle of Wild Turkey from a lower shelf and a shot-glass and headed over to him. "Sure thing, just gotta see your I.D."

He grabbed his wallet, pulled out his driver's license, and handed it to her. She eyed up the card with special interest. "Dean Winchester, huh?"

"That's me."

"And you just turned twenty-one in January. Well…" she handed the I.D. back to him, "happy belated birthday."

Dean stuffed the card back into his wallet and returned it to his back pocket. "Thanks."

"I'm Jane, by the way."

"Oh. Well Jane, nice to meet you."

She put the shot glass down on the counter and filled it with whiskey and Dean picked it up and immediately shot it down, grimacing a little at the burn sliding down his throat, and then motioned for another. "So…" She filled the glass again, her smile turning a bit smug. "Only twenty-one and already a heavy drinker. What is it? Girlfriend, school, job, or…" she leaned in towards him, "…other?"

He tossed back his second shot. "I don't really wanna talk about it. But I'll have another drink."

She smiled wider, cocked her head to the side, and opened her mouth as if she was going to say something, but then a middle-aged man from the other side of the bar with a scruffy brown and gray beard and shaggy, unkempt hair called out to her. "Hey, Jane! You gonna spend all night talking to Pretty Boy over there or ya gonna get me my screwdriver already?"

She frowned at the guy and then poured Dean his next shot and winked at him. "I'll be right back." She turned her back on Dean, then walked back over to the shelves of liquor and picked up the bottle of vodka. "Yeah, Eddie, I'll get you your drink, just keep your pants on!"

Dean scowled at the Grizzly Man Adams wannabe for calling him "Pretty Boy," but decided not to pick a fight. Instead, he stared down at his shot and let his mind wander. _Take me._ He pictured Sam as he looked, kneeling in front of him on the bed, when he'd said that. _Take me. Take me, Dean. Please._ It echoed in his ears, the sound of it and the look in Sam's eyes when he'd said it threatening to drive him mad. He gulped down his shot. Sam wanted him to be his first, or at least he thought he did. Maybe he wanted it now, but what was going to happen five or ten years down the line when he'd been places on his own, knew more, and saw that there was a big world out there full of beautiful women (and guys too, if he wanted that,) willing to give him anything he wanted and that he didn't have to limit himself to just fooling around with his brother? What would happen if Sam got a girlfriend who he was serious about and she asked him about who he'd been with before her? What was he going to do, lie? He'd almost certainly have to because who would stay with someone after admitting that they'd lost their virginity to their own brother? Or what about when Sam realized that he was thirty and still unmarried with no children, unlike the life he'd always dreamed? How would he feel then? Hell, how would he even feel next year when he graduated high school and had the chance to go to college? With Sam's good grades, he was sure that his little brother was going to get his pick of any number of schools, probably even ones that would pay him to go there. Sam would like that, he'd want to get to stay in school and make friends, pretend like he was normal and like all he'd had to worry about in the past few years was pimples and prom dates like the rest of them. That kind of shit would make Sam happy.

But, in the meantime, Dean was holding him back by being a selfish, short-sighted dick. He remembered what Sam had said to him the night he'd finally agreed to be with him: _Dean, you're not wrong for wanting this. I want it, too. So damn bad. And then I see you going to some slut instead of me and it makes me think of all the things she's getting from you that I can't have and it makes me…I can hardly stand it; it's all I can think about. You are all I can think about. You're not hurting me by wanting to touch me, I want you to. I only want to be with you. Come on Dean, please. This is the only way we can be happy._ Since that night, Dean had hoped that if he agreed to be with Sam, if he could only give him what he wanted and made him happy enough, then maybe Sam wouldn't ever want to leave this life. Maybe instead of finding a wife or going to college, Sam would want to stay with him and Dad. Maybe eventually the two of them could even start going on hunts on their own, away from the prying eyes of their dad, where they'd get to rent a room of their own and not have to bite their fists or bury their faces in a pillow to muffle the sounds they made when they pleasured each other. Maybe, when they were on a hunt far enough away, they wouldn't have to hide at all.

And back there at the house, he'd come so close, he could have had everything he'd ever wanted. Sam was offering himself to him. _Take me, Dean. Please._ God, Sammy had wanted it so much, he really had. He'd seen it in Sam's eyes, like having sex with him was some kind of dream come true. Who dreamed about having sex with their own brother? Not normal kids, that's for sure. And they weren't normal. Fuck, they were actually about as far from 'normal' as two people could get. They would be thought of as freaks, even in hunting circles, for what they'd been doing for the past five months if anyone found out. Their dad would hate him for loving Sammy this way. He'd accepted those consequences though, at least for himself. He felt a pull towards Sam that he couldn't understand, but he knew that it was bigger than him and that no matter how hard he tried he couldn't fight against it. At least, not when Sam wanted it too, not when he'd lie beside Sam at night and feel the sexual tension rolling off his body, or hear him jerk off in the shower and know he was thinking about him while he did it. He'd tried resisting already and it was a dead end. And since before they were even together, Sam had spent several hours assuring him that he felt the same way, that he was willing to accept whatever consequences came from their relationship, and that he wanted him no matter what happened. Dean just wished he could stop feeling like he was ruining Sammy's future by believing it.

"Sorry about that." The bartender came back over to him and filled his empty shot glass. Thank god; he'd gone long enough without a drink. "Hope you weren't hurting too much for cirrhosis without me."

Dean smiled at her and downed his fourth shot, noticing that it hardly burned anymore. "Thanks."

"Sure thing, handsome. You want something else, maybe a little less strong?"

"Nah, keep it coming."

She poured another shot. "So, I take it you're not from around here?"

"What makes you say that?"

"Well, we're a pretty small town and I've never seen you before. To tell you the truth, we don't get very many outsiders, especially ones as good-looking as you."

Dean chuckled and took his shot. "So, you're telling me your town is just a bunch of uglies, huh?"

She laughed and motioned her head subtly towards the other end of the bar, where a group of middle-aged men, including the guy who had called him a pretty boy, were all sitting and talking amongst themselves. "That's about the average age of guys in this town." She refilled his glass. "We're an old milling town, mostly died out about fifty years ago but some of us are still here."

"Well, if the town is so dead, why are you here?" Her eyes once again flashed with surprise and although she kept a smile on her face, Dean could tell he'd made her uneasy. He held his hands up in apology. "Sorry; it's none of my business."

"No, no, it's okay, really." She ran a finger down her jawline as she looked off in space for a moment, appearing deep in thought, then turned around, grabbed a second shot glass, filled it, and threw it back. "I'm here staying with my aunt and uncle until I can save up enough money to go somewhere else and get a place of my own. My parents, well, they died a few months ago."

"Oh." Dean picked up his glass and stared into it, feeling a little like a jerk. "Sorry."

"It's okay." She poured herself another shot. "They died in a car accident. There was this sudden fog that covered the highway and – well, a few people died, it made the papers." She took her shot and then smiled at him extra wide. "Anyway, so now I'm here. To tell you the truth, I never imagined that I'd end up here, you know, in this small town, working at a bar, but I guess that's just the way life is."

Dean tossed back his shot and welcomed the warmth. It no longer burned at all and he was beginning to feel a nice, fuzzy feeling all over. "Well, you seem to be taking this whole thing a lot better than most people would."

She shrugged. "I have my good days and bad days. And I have my regrets too, like, I'd gotten into a big fight with my mom before they left over laundry, isn't that the stupidest thing? So I didn't hug her before she left the house."

Dean shook his head. "She knew. People fight about stupid shit all the time, but in the end, they know. At least the important stuff."

"Yeah, I know. Well, logically I know. But sometimes, when I think about it, in my heart I'm not so sure."

"She knew."

"Yeah, I'm sure you're right. It was a dumb fight. At least it wasn't over something really awful. I don't know how I'd be able to make it through the day, let alone the rest of my life, if I had said or done something really terrible."

Dean didn't have anything to say about that. Grieving people obsessed about their final moments with loved ones. He'd seen enough of it to know. The sound of her voice broke him from his thoughts when he realized he'd stopped listening to her.

"…least I didn't tell her I wished she wasn't my mother or something. But still, I'd give anything to have at least one more minute with her. You know, tell her I love her, that I appreciated everything she'd done for me. I'd give anything to have her back so I could show her how much she means to me."

"I guess I never seriously thought about it, but I think I get it. If things ended for me right now…" Sam's last memory of him would be rejection, he'd spend the rest of his life thinking that Dean didn't want or love him. And if things happened the other way around… An image unwillingly crowbarred its way into his head, of Sam wrapped up on a funeral pyre, Dean watching the flames licking at his young body, and knowing that Sam had died thinking that Dean… He shut the memory forcefully from his consciousness, like a door being slammed shut. There was no way he'd be able to live with that kind of regret.

She shook her head. "I'm sorry; you just came here to drink and forget about whatever it is bothering you and here I'm just going on about my problems."

"It's okay. You know, to tell you the truth, I see a lot of death in my line of work, families split up in some pretty gruesome ways. And in the end everyone has their regrets. I guess no matter what you do, there's always gonna be something you think you did wrong. I don't know, maybe in the end, you know, it comes down to it, the only thing you can really do is just make the decisions you think you're gonna regret the least." He sat and stared at his empty shot glass as he thought about that. And, in the end, what was he gonna regret the least when it came to Sam? That really depended on how and when it ended and, as a hunter, being able to predict that was about a hundred times more difficult than with most.

She poured him another shot. "On the house."

"Thanks."

He picked it up and shot it back and then after he put down the glass he saw Jane grabbing onto the edge of the bar, squinting at him and giving him a lopsided smile. "Something tells me we're not talking about me anymore."

Shit. On instinct, he shot her a confident, flirtatious smirk. "Oh no, don't."

She giggled playfully. "Don't what?"

"I can tell right now, you wanna go all Robin Williams from Good Will Hunting on my ass. All that's missing is for you to start telling me it's not my fault about ten times."

She laughed and shook her head. "Look, Dean, I don't know what is or isn't your fault, but whatever it is that's bothering you, whatever you regret or think you're going to regret, let me just say this one thing: if there's one thing I've learned from all this with my parents, it's that life can change at any second, whether we want it to or not." He nodded; she was right, probably way more than she knew. "So, I guess you're right, everyone's got regrets, but I don't think it's all about making the decisions you think you're going to regret the least. To do that means that you're constantly gambling on what's going to happen in the future for you to regret, possibly pretty far down the line if you're already thinking about death. I think it's all about deciding what's going to benefit the most people now, what's going to make the people you love happy, and what's going to bring you the most love and happiness now. Leave those burial-side confessions for another day."

Dean stared at her thoughtfully and then shook his head. "You know, for someone who seems so down to earth, you're kind of a hippy chick, you know that?"

She blushed and laughed nervously. "I'm sorry, that sounded hokey, didn't it?"

"No! No, it's alright…" He tried on a reassuring smile. "It doesn't sound hokey. Actually," he let out a little nervous chuckle, "it sounds pretty damn realistic."

She poured them both another drink, then picked up her shot glass and held it out in a gesture of a toast. "To living in the here and now."

He grinned and lifted his glass. "I'll drink to that."

They clinked shot glasses and quickly threw back their shots. After she lowered her shot glass, she leaned over and rested her elbows on the table, using her arms to squish her breasts together and it was then that Dean noticed that she actually had a really nice rack. "Look, Dean, you seem like a nice guy. I know you don't want to talk about it, but whatever's bothering you clearly has you feeling pretty depressed." She leaned in more and lowered her voice. "How about we do something about it? My shift doesn't end for a while, but I can get one of the guys in the back to cover for me. My aunt and uncle are out of town until Monday. We could leave right now, go back to my place. Maybe I could cheer you up a little?"

Dean raised his eyebrows in surprise. "Oh."

"Honestly, I could use a little bit of fun too; it's been a few months since I've had any. What do ya say? I'm very good with my hands, mouth…etcetera."

"Oh. Um…"

He pictured himself in some unfamiliar bedroom with this woman, lying down on the bed with her straddling him, his thick cock buried to the hilt inside her wet pussy as she bounced up and down on him, her face contorted in pleasure as she cried out. It felt wrong and unappealing. Because, really, whether it felt good or whether it was fun at the time, it was just a fuck, plain and simple. She was sort of hot and he even kind of liked her personally, but in the end he'd leave her bed, forget her name, and then still be left feeling empty and lonely, prowling for the next hour of fulfillment through physical pleasure so the cycle could start all over again. And all the while, Sam would be sitting alone in their motel room brooding with a broken heart, probably like he was right at that moment while he was out at a bar and getting drunk and hit on by chicks. But this wasn't what he wanted. He wanted Sam; to go back home to him and see his face again, to hold him and fall asleep beside him. _Take me, Dean. Please._ He wanted to take him. God help him, he wanted it more than he'd ever wanted anything in his life, to love Sammy, to show him just how much he meant to him while he still could.

He grinned and stared down at the table embarrassedly. "You know, normally I'd try getting you back to your place so fast it'd make your head spin, but…I'm sorry, I'm actually already spoken for."

She frowned. "Is it serious?"

"It actually is. But I'm sorry; I hope you find someone to have fun with. I should probably just pay my tab and go."

Still looking wildly disappointed, she handed him his bill. "Well Dean, like I said, life can change pretty suddenly. So…" she slipped a folded piece of paper over to him, "if anything changes, look me up, okay?"

He took the number and shoved it into his pocket, more out of politeness more than anything else. "Thanks. Good talking to you." With that, he slapped enough cash down on the table to pay for his tab and a generous tip, winked at her, turned around, and walked out the door.


	3. Chapter 3

When Dean got home, Sam was dressed in a t-shirt, baggy green and white plaid flannel pants and socks, sitting on the living room couch and staring blankly at the TV. Dean closed the door behind him, shrugged out of his coat and held it in his hand as he stood awkwardly in the doorway staring at his brother.

"Hey Sammy, I'm home."

When Sam turned towards him, his eyes were dry but red and puffy and his cheeks were shiny; he'd obviously been sobbing for a while. He gave Dean only the briefest glance and then looked down at the couch, then back to the television for a second, as if he didn't care that he was home. "Hey Dean." Fidgeting uncomfortably under Dean's stare, it was pretty apparent that Sam was only pretending to watch television and after a minute, he picked up the remote, shut off the television, sighed, and stood up. "I'm gonna go to bed, I guess I'll see you in the morning."

"Sam, wait." Dean quickly walked across the room and stood in front of Sam, then threw his jacket over the armrest of the couch behind him. "Sam, I'm sorry."

"Me too," he mumbled. "I shouldn't have sprung it on you like that. I just…I don't understand. I thought –" his voice broke and he looked down and away, but Dean could still see the few new tears wetting his face. "I thought you'd want to."

Dean quickly reached up, grabbed Sam's face, and turned it towards him. "Hey – hey – hey – hey, Sammy" he rubbed his thumbs across Sam's cheeks, wiping the tears away and smearing the shiny, wet tracks. "Sammy, look at me, look into my eyes. I do want to, so much. I'm sorry; I know I was being a major dick earlier, I shouldn't have run out like that. I just needed some time to think. But I do want you; don't ever think I don't. Look into my eyes and tell me if I'm lying."

Sam's solemn eyes searched Dean's for a moment. He nodded and then wiped an arm across his face, completely clearing off any moisture lingering there, and sighed. "Well, I guess if you want us to wait a while, I can do that. But whenever you think is a good time, well, I'm ready whenever you are."

Dean took his hands away from near Sam's face and put them awkwardly to his sides. He thought about what he wanted to say next and suddenly felt stupid and clumsy. He didn't know how to speak or where to put his hands, his heart raced and he felt a lump forming in his throat like some virginal pre-teen. "How about now?"

Sam's eyes grew wide and his mouth dropped open. "Really? Are you sure? I don't want you doing this just for me if it doesn't feel right to you."

Dean took another step into Sam's space so that their faces were only inches apart. "Do you want this, Sam? Are you absolutely sure you want your first time to be with me?"

Sam nodded. "Yeah, Dean. I'm sure."

"Then I'm ready."

Sam stood still for a moment, looking thoroughly shocked and unsure of what to do next. Then, shyly, tentatively, he reached out and stared at his hand as he rubbed it up and down Dean's bicep. "Okay, well, uh…"

He leaned in slowly, closed the three or four inch gap between their faces and kissed him. It was slow, unhurried, and felt as unpracticed and awkward as if it was the first time Sam had ever kissed anyone. Dean moved his experienced mouth against Sam's, trying to lead the kiss and help Sam's lips get into a rhythm, but he couldn't help the excited tightening in his throat and stomach that made him feel like he was a little off his game. When getting ready for sex he was used to feeling excitement, but it was never like this; he never felt awe, or love, or this stupid nervousness he had in his hands that he wouldn't be able to touch Sam right, or the strong anxiety he felt over not being able to satisfy him properly. As they kissed, he put his hands experimentally at the sides of Sam's waist and pulled him in so their bodies could touch and then Sam followed suit, shyly touching Dean the same way. Dean broke the long kiss, gave him a couple more pecks on the lips, and then laid a soft, gentle kiss on the little mole beside Sam's nose.

"You wanna take this to the bedroom, or you wanna have sex on the couch?"

Sam blushed. "Bedroom."

"Okay." They disentangled themselves and then Dean grabbed Sam's hand. "Come on," he whispered and then tugged, leading them to the bedroom.

When he opened the door and pushed inside, the room was unlit, save for a lamp beside the bed that cast dim light and shadows around the room. There were two beds in the room: Sam's, which was in the far left corner and almost always made because it was rarely slept in, and his, which lay right in front of them, unmade and with the condoms and lube still sitting in the exact same place they had been when he'd left. Beside the bed, all of Sam's clothes, save for the t-shirt he was wearing, were still on a crumpled heap on the threadbare carpet. Dean quickly threw off his boots and then heard the sound of the door clicking as Sam closed it behind them. Sam walked around him and then stood facing him at the foot of the bed, his eyes wide and a little scared looking, but his erection still tenting his pants noticeably as he lifted his shirt over his head and threw it to the ground. Visibly trembling fingers then reached down and grabbed the waistband of his pants, but Dean walked over to him and put a hand over Sam's, stopping him.

"It's okay, Sammy." He leaned in and gave Sam a comforting, chaste kiss on the mouth. "You don't have to get naked for me right away; we can go as slow as we want tonight."

"Yeah, I know, I'm sorry Dean, I'm just so nervous."

"I know. I am too."

Dean slipped his own shirt over his head and threw it to the ground next to Sam's. His eyes went wide in awe as he dragged them up and down Sam's lean, lithe, slightly trembling body. He slowly and uncertainly put his hands on the sides of Sam's waist. This shouldn't feel so awkward to him; he'd had sex before, loads of it, with a lot of different people. More than that, he'd messed around with Sam so many times already, going much further than just touching each other with their shirts off. But this was different; he was about to make love to Sam – his brother, his best friend, his partner in everything. Nothing he'd ever done was even remotely like this. He craned his neck forward and slowly licked Sam's lips and Sam responded instantly by leaning in and beginning to chase his mouth. Their mouths slid together and soon found a slow rhythm, working in time with one another as they sucked on each other's lips and tongues. Dean pulled Sam's body in towards him and Sam willingly stepped in to him so that the smooth skin of their chests could touch and then Dean moved his hands slowly up and down Sam's back in a comforting way, hoping to help calm his brother's nerves. Sam's hands were gliding up and down Dean's biceps, but then moved slowly down his sides and to the waistband of his jeans. Fingers dipped just barely inside and felt along the v-cut of muscle above his hips, then travelled along the waistband to the front of his jeans and felt along the thin line of fine, blond hair there. In the next moment, Dean's erection felt less restricted in his pants as Sam undid the button and zipper. Sam seemed more self-assured and he was no longer shaking, but his movements were still tentative and slower than usual and it seemed pretty clear to Dean that he needed to take the lead. He pushed on Sam's chest and Sam let himself fall backwards onto the bed, his feet still planted on the ground. Dean climbed on top of him, straddling his hips, and as Sam's serious and aroused face looked up at him, his longish hair making a messy circle around his head, Dean reached up and stroked his fingers along Sam's jaw.

"God, look at you, so gorgeous." He moved in and licked along Sam's lips, then looked down at his brother. "I love your body, Sam." He ran his hands across the hard, muscular planes of Sam's pecs, down to the hard ridges of his stomach, briefly touching the tip of the hot, hard bulge in his pants, then back up to his chest where he pinched each of Sam's nipples between his thumb and forefinger and then tweaked them just a little. "You're so fucking hot for me."

He moved his mouth to the side of Sam's jaw and opened his mouth wide to lay a kiss at the sensitive flesh and then sucked lightly and licked, inhaling the clean smell of Sam's skin and feeling his slight stubble under his tongue. "I am," Sam whispered, "want you so much –" Dean nipped the skin and Sam made a little moan and then hissed, "No hickies," in a raspy voice.

Dean nodded against Sam's skin. He actually suspected that Sam would like his skin to be sucked and bitten just enough to give him a few bruises, so it was really more of a reminder than anything, cautioning him about what he already knew: they couldn't leave any marks or signs of what they did to each other. He moved his mouth down the side of Sam's neck and over his smooth chest and stomach, slowly licking, kissing, and nibbling the smooth skin and little scars along the way. He loved giving Sam such elaborate attention and getting to hear his breath quicken, then come out in little gasps and pants as he thoroughly licked and sucked every part of his chest and stomach. When he got to the waistband of Sam's pants, he had to get off the bed and kneel in front of Sam on the floor. Sam spread his legs to accommodate Dean between them and once he was settled, he saw that the very tip of his hard, red head was peeking out from underneath the waistband and a small puddle of clear, slippery pre-cum was collecting on his stomach. Mm, no underwear. He grabbed Sam's pants and tugged, thoroughly enjoying the way Sam eagerly arched his back to make it easier for him. Once they were pulled down over his hips, he could see Sam's fully hard, flushed cock resting against his stomach. He grabbed it, lifting it away from the slick pool collecting on his stomach, and then brought it close to his mouth, where he could smell the strong musky odor of pre-cum that still leaked from the head. As he touched his tongue to the head, he looked up and saw Sam watching him and then their eyes locked as he moved his hand in a circular motion, rotating Sam's cock around his tongue.

Sam's eyes burned bright and his cheeks flushed as he watched. "Oh yeah, god Dean, you look so hot like that." Then Dean jammed his tongue into the slit and Sam's body began to shake and he threw his head back and let out a filthy moan. "Ooh – god – Dean…"

"What is it, Sam? You want me to suck your dick?"

In response, all Sam seemed to be able to do was let out an unintelligible moan that sounded so hot and needy, it made Dean leak a little pre-cum into his boxers. Dean took his tongue off of Sam but kissed the head and then opened up and felt the velvety-soft skin slide past his lips and into the hot, wet heat of his mouth. He wrapped his hand around the base and jerked him in time to his mouth as he bobbed slowly up and down Sam's cock, making his lover moan, thrash on the bed, and grab handfuls of sheets. And, like when he'd done this before, it wasn't long before Sam's hands were on his head, tangling in his hair, and trying to push him off.

"Stop! Dean, stop – oh – oh god – stop!" Dean pulled back and Sam was instantly covering his hand on the base of his cock, squeezing hard to stop his orgasm. "Oh god, that was close."

"You don't want me to make you come?"

Sam shook his head. "Not yet. I wanna wait until we're…well, you know."

If Dean wasn't so turned on at the time, he might have actually laughed at Sam at that moment. The kid was minutes away from having sex and still couldn't say the word out loud. "Are you sure? I'll bet I can make you come twice."

"I'm sure."

"Okay." Dean crawled back up on the bed and gave Sam a quick kiss on the mouth. "Are you ready?"

Sam nodded. "Definitely."

Sam's hands reached down to Dean's pants and gruffly pushed them and his boxers down over his thighs, but then Dean got up off the bed so he could take his pants and boxers down the rest of the way and slip off his socks. Then he went to the foot of the bed, grabbed the waistband of Sam's pants and pulled them the rest of the way off, then took off his socks for him one at a time. He looked down at Sam's fully naked body; the muscular legs, his red, straining erection, his smooth, young skin that looked a little orangey under the soft glow of the lamp and was covered in a thin sheen of shiny sweat, his soft, pink lips, his wanting, pleading, trusting eyes. Sam wanted this, he wanted him, and he trusted him to make it good for him. Dean leaned over Sam and grabbed the condoms and lube from where they still lay on the bed above Sam's head and then stood back up.

"Turn over for me."

Sam immediately did as he was told, getting on his hands and knees and then he crawled up the bed, towards the headboard, to give Dean some room to get behind him. Dean got on his knees behind Sam, set the box of condoms beside them, and opened the bottle of lube.

"I have to prepare you to make sure I don't hurt you, okay?"

"Yeah, I know. Do it."

Dean blinked in surprise, but only for a second. Yeah, of course Sam knew what to do; like everything else, the kid had probably researched to death all about how to have gay sex during the past several weeks before approaching him about it. He wondered if Sam went to an educational website or if he just watched some gay porn to figure it out. Dean leaned in and laid a line of kisses down Sam's lower back and then playfully nibbled one of his butt cheeks. Maybe he'd ask later and find out what else Sam knew. He squirted a generous amount of lube onto three of his fingers, then brought his forefinger to Sam's entrance and began petting around it, seeing how the muscles began to twitch and contract under his touch. He kept rubbing for about a minute until Sam started to moan and the muscles began to pulse and spasm. Oh god, he wanted to be inside Sam's ass so fucking bad, he could hardly stand it. He pushed his finger in all the way to the webbing and then began to slowly move it in and out. The muscles felt tight, but Sam didn't seem to feel any discomfort; instead, he rocked back on his finger.

"Mm, Dean, I'm ready, put another one in."

Dean raised an eyebrow. "Done this before?"

Sam hesitated. "Tried it a little the last couple of weeks."

He thought about Sam kneeling on their bed alone and fingering himself and, fuck, it made him so hot that he actually growled. "Really? Oh fuck, that is seriously hot. Watching you do that to yourself is so going on the 'To-Do' list for later."

He pulled the first finger out and then watched in wonder and curiosity as two of his slippery, wet fingers disappeared inside of Sam's body. Sam's muscular walls tightened up around them and he heard him stifle a little groan, so he stilled his fingers and let him get used to the girth and ran a soothing hand along Sam's back.

"It's okay; try to relax."

When he felt the muscles loosen around his fingers a bit, he began sliding then in and out and then moved them in scissoring motions to open up Sam further. At first, Sam stayed perfectly still and held his breath as he moved, but after a couple of minutes began rocking back and forth on his fingers, his moans growing increasingly loud and urgent. "Oh god – I'm ready, take your fingers out, I wanna face you."

"Fuck! I want to, Sam, I want to so fucking bad." He kissed the middle of Sam's back, along his spine. "Just take one more first; I don't wanna hurt you, babe."

When Dean added the third finger, he moved them gingerly, moving the tips just a little bit and changing the angle ever so slightly every once in a while. He'd heard about a spot that guys had deep inside them that would make Sam feel really good if he could find it.

"Dean! God, Jesus Christ, I'm ready! Please!"

Sam hadn't shuddered or shown any signs that he'd hit anything special inside of him; he was just impatient and wanted to have sex. And so did Dean; his cock was leaking so much pre-cum that there was a thin string of it connecting the head of his cock to the bedspread underneath them. He pulled his fingers out and wiped them on the bedspread and Sam flipped himself over so that he was lying on his back and facing him, his cheeks flushed and his cock so hot, hard and swollen that it looked like he was about to come any minute. Dean opened the box of condoms, then took out a strip of them, ripped one off and tossed the box to the floor. Once he had the condom rolled all the way down to the base, he drizzled a little more lube onto it and then inched forward on his knees into Sam's space. He picked up his legs and put them on either shoulder, grabbed Sam's ass, firmly gripping a cheek in each hand, and lifted his pelvis in the air. Sam's breath hitched and when Dean looked up into his little brother's face, he saw that he was once again looked wide-eyed and scared.

"Sammy? You okay?"

"Y-yeah, I'm fine."

"Are you sure? We don't have to do this; if you want to stop, just say the word. I promise, I won't get mad or anything."

Sam closed his eyes, nodded, and took a deep breath. "I know. It's a little scary, but I want to. Go ahead, put it in."

Dean leaned forward and gave Sam a soft, reassuring kiss on the mouth, then sat up on his haunches, lined himself up, and slid forward. As he felt the head push past the first ring of muscle, he closed his eyes and let out a soft moan. Fuck, he was tight, so much hotter and tighter than any woman he could remember sleeping with. He moved forward inch by inch letting Sam slowly adjust until he was all the way inside, buried to the hilt, and then stayed completely still, although it took all his willpower not to move. Even with the condom, just being inside of Sam and feeling the muscles gently squeeze his cock felt amazing. Sam stared up at him and nodded his head, giving him the go-ahead to move. At first, Dean slid out slowly, not daring to move too much and then slowly eased himself all the way back in. More than anything, he was terrified of hurting Sam by moving too fast or pushing in too hard and he didn't want to mar Sam's memories of his first time by causing him any pain.

But Sam, however, didn't seem to have the same concern. After about five minutes, he pushed himself down hard on Dean's cock. "Faster!"

Dean began sliding out a little further, pushing in a little harder, and moving a little faster. And, damn, did it feel good; Sam was plenty slick from all the lubrication and he felt hot, tight, and fucking perfect around him. Sam screwed his eyes shut and made little grunts of pleasure and his hard cock twitched against his belly and leaked pre-cum over the already sticky skin. Seeing Sam enjoy it so much practically pushed Dean over the edge and before he knew it he was pushing into him faster, harder, rougher, and babbling all sorts of dirty things.

"Jesus Sammy, you feel so fucking good, you're so tight, so goddamn perfect, better than any pussy I've ever had, fuck, you're gonna make me come so fast and hard inside you –"

Surprisingly, the more Dean talked, the more worked up Sam got. His breathing became heavier, his moans louder, and then he used his arms to brace himself and started pushing his ass down harder on Dean's dick. Dean felt himself start to get close. He started changing the angles of his thrusts, still looking for that spot inside Sam that would make him –

"Oh my god!" Sam screamed out and arched his back on the bed. "What was that?"

"Looks like we found your sweet spot." Dean kept moving at the same angle, making sure to hit the same spot over and over again with each thrust, feeling proud of himself for finding Sam's prostate the first time they had sex and loving the filthy moans Sam made as he thrashed and grabbed onto everything he could, including bed sheets, the headboard, and Dean's knees. He felt his orgasm quickly rising within him and knew that no matter what he did, he wasn't going to be able to delay it for much longer.

"Shit, I'm so close, Sam. Can you come just like this, just with my cock? I know you can, I know you're so fucking close. Wanna watch you mess yourself up, just for me, just because I can make you feel so good this way."

Sam arched his back, made a loud, unintelligible noise, and came all over his chest and stomach and just the sight of that alone had Dean coming hard and fast, filling up the condom just a few thrusts later. After he felt the last satisfying tug of his orgasm, he carefully grabbed the base of the condom, gently eased himself out of Sam, then tied the condom off and threw it into the nearby trash and, still panting, collapsed onto the bed beside his lover. Sam brought the corner of the bed sheet to his chest and stomach and wiped it off, then turned onto his side, threw and arm over Dean, and kissed him on the side of the mouth. Dean turned his head towards Sam and then his body followed, throwing an arm over his lover and bringing him in close.

He laid a kiss on Sam's lips and then Sam turned back onto his back and stared blankly at the ceiling. "I'm not a virgin anymore."

Sam's face was expressionless and his voice was flat and toneless and Dean raised himself up on one elbow to get a better look at him. "Any regrets?"

Sam turned to him and grinned. "Hell no. I just still can't believe it, feels a little unreal." He laid still for a moment, looking deep in thought. "Hey, Dean, can I ask you a question? What changed your mind?"

Dean turned leaned over, turned off the lamp and laid back on the bed. "Goodnight, Sam."

They laid in the dark for a few minutes and then, "Dean?"

"Yeah?"

"Can we do it again?"

"Now?" Fuck, he remembered what it was like being a horny teenager, but that round of sex they'd just had was long and exhausting. And Sam's first time…sure, he was gentle, but the kid had to be sore.

"Uh, no, I meant, well…ever?"

In the dark where Sam couldn't see, Dean smiled. "Yeah, Sam, whenever you want; I'm ready whenever you are."

.

Thanks for reading, if you liked it please send me a review!


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